A graduate of Dartmouth in 1801, Daniel Webster (1782-1852) was adopted as the College’s “second founder” when in 1818 he eloquently and successfully defended its original charter in the United States Supreme Court, arguing against those who wished to have the private institution restructured as a state university. Webster eventually served as a United States congressman (1813-17), senator (1827-39 and 1845-50), and secretary of state (1841-42). The most successful portraitist of America’s early national period, Gilbert Stuart had mastered the British grand manner style during an eighteen-year stay in London and Dublin. After returning to America in 1787, he worked initially in New York and Washington, painting likenesses of the nation’s most prominent citizens and political leaders, including George Washington. After 1805 he worked in Boston, where he painted this dashing and penetrating likeness of Webster. As is evident in this work, Stuart took tremendous pleasure and interest in capturing a sitter’s likeness and especially in his later years often chose not to complete the background, which he viewed as of secondary importance. Although unfinished, this portrait is remarkable for its vibrancy and ease of execution. It is also among the most sympathetic images of Webster, who was depicted by artists more often than any other figure of his generation. The countless portraits painted later in the great statesman’s career tended to accentuate, sometimes to the point of caricature, his imposing public presence. This portrait, by contrast, captures a gentler and more introspective side of the legendary “Black Dan,” portraying him as an individual capable of private emotions as well as public pronouncements. It is one of hundreds of images of Webster and objects associated with him owned by Dartmouth College.